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If the sale is via the internet and the California seller has no Illinois location, then no, you don't need to charge Illinois sales tax. You'll need to consult California tax law to know whether to charge him California tax, but probably don't need to charge it either.

If the sale is in person in California, then yes, you should charge him California sales tax.

If the sale is via the phone you could probably get away with calling it an internet sale and skip the tax, although it depends more on California tax law than Illinois tax law.

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Q: Should Californian business owner charge a buyer from Chicago sales tax for an item that will be resold in Chicago and the buyer do not have a valid seller's permit?
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